Literature DB >> 24706539

Desymmetrization of diolefinic diols by enantioselective amino-thiocarbamate-catalyzed bromoetherification: synthesis of chiral spirocycles.

Daniel Weiliang Tay1, Gulice Y C Leung, Ying-Yeung Yeung.   

Abstract

A facile, efficient, and highly diastereo- and enantioselective bromoetherification of diolefinic diols has been developed using an amino-thiocarbamate catalyst. Further manipulations of the bromoether products enabled entry into a new class of spirocycles which are distinctively lacking in the literature.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis base; asymmetric catalysis; chemoselectivity; cyclization; furans

Year:  2014        PMID： 24706539     DOI： 10.1002/anie.201310136

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO2-Capture: Discovery, Development, and Mechanism.

Authors:  Roozbeh Yousefi; Thomas J Struble; Jenna L Payne; Mahesh Vishe; Nathan D Schley; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-12-24       Impact factor: 15.419

2.  Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

Authors:  Bardia Soltanzadeh; Arvind Jaganathan; Richard J Staples; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-25       Impact factor: 15.336

3.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

4.  Solvent and catalyst-free bromofunctionalization of olefins using a mechanochemical approach.

Authors:  Jonathan Wong; Ying-Yeung Yeung
Journal:  RSC Adv       Date:  2021-04-12       Impact factor: 3.361

5.  Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.

Authors:  Nastaran Salehi Marzijarani; Roozbeh Yousefi; Arvind Jaganathan; Kumar Dilip Ashtekar; James E Jackson; Babak Borhan
Journal:  Chem Sci       Date:  2018-01-02       Impact factor: 9.825

6.  Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.

Authors:  Jie Luo; Qingxiang Cao; Xiaohui Cao; Xiaodan Zhao
Journal:  Nat Commun       Date:  2018-02-06       Impact factor: 14.919

7.  Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols.

Authors:  Zhigao Shen; Xixian Pan; Yisheng Lai; Jiadong Hu; Xiaolong Wan; Xiaoge Li; Hui Zhang; Weiqing Xie
Journal:  Chem Sci       Date:  2015-08-27       Impact factor: 9.825
  7 in total

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